Water → 3-Bromo-2,5-dimethoxybenzaldehyde

HRID 1794490Notes

Reaction equation

HRID 1794490 reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6].CI.[C:15]([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[Br:1][C:2]1[C:3]([O:12][CH3:15])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 7358183-Bromo-2-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 9310963-Bromo-2,5-dimethoxybenzaldehydeYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 50 (10 g, 43 mmol), Methyl Iodide (7.3 g, 52 mmol), and K2CO3 (12 g, 86 mmol) in acetone (200 ml) was heated to reflux. After 4 hr, the reaction was cooled, poured into water and extracted with ether. The ether layer was dried concentrated and the product was purified by silica gel column chromatography (10% EtOAc/Hex) to give 51 as a solid (7.0 g, 67%): Mp=62–64° C.; 1H NMR (CDCl3) δ 10.32 (s, 1 H), 7.38 (d, 1 H, J=2.8 Hz), 7.28 (d, 1 H, J=3.2 Hz), 3.93 (s, 3 H), 3.82 (s, 3 H); MS 245/247 (M+H)+

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted with ether
  3. dry with materialThe ether layer was dried
  4. concentrationconcentrated
  5. customthe product was purified by silica gel column chromatography (10% EtOAc/Hex)

Sources & evidence

ORD record
ord-a6968c07a8e24a93bb5224d45e371a4c
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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